


Five Times Oswald Procures Lingerie, and One Time Jim Procures it For Him

by pamdizzle



Series: Dreams of Lace and Satin [1]
Category: Gotham (TV)
Genre: Angst, Canon Compliant, Diverges from canon at 4x21, Edward Nygma - Freeform, First Time, Frottage, Happy Ending, Lingerie, M/M, Masturbation, Poor Jim, Romantic Gestures, Self-Esteem Issues, Sex, Slow Build, gobblepot, mentioned - Freeform
Language: English
Status: Completed
Published: 2018-05-07
Updated: 2018-05-15
Packaged: 2019-05-03 17:54:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 18,159
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14574396
Author URL: https://archiveofourown.org/users/pamdizzle/pseuds/pamdizzle
Summary: Harvey jokingly provides Oswald with men's lingerie, but the joke's on him because it's the gift Oswald never knew he needed.I know it sounds like crack, but it's not. I promise.This is a story about self love and acceptance. It just so happens to contain copious amounts of porn...it’s just a coincidence, a quinky-dink, if you will.





	1. Harvey’s Blunder, Oswald’s Wonder

**Author's Note:**

> This is my first fic in this fandom. I haven't written anything for any fandom in a while, but this plot bunny snuck in to the thinky-thoughts garden and just wouldn't die. So, here we all are.
> 
> Should be about six chapters, hopefully all posted over the next two weeks.

The first time isn’t Oswald’s fault. Though, he hesitates to credit Bullock for anything he enjoys so thoroughly. He refuses to be grateful, but he must admit, if only to himself, that if Jim’s unkempt partner hadn’t intervened Oswald never would have discovered this one, small indulgence.

He’d been leaving the precinct the day it happened, having just handed off Jim’s invitation to attend opening night of Oswald’s, when fortune had found him in the form of Harvey Bullock. The detective had been smirking, and his eyes had only shone with greater mirth the moment they had alighted upon the gangster exiting the lobby.

“'Ey, Penguin!” He’d called raucously enough to garner the attention of anyone within earshot. “Found something that might just be up your alley!”

Without any further warning, his vision had been quickly obscured by something soft and black. Oswald had grit his teeth, quietly seething as laughter rose up around him. With measured breaths, he had peeled what turned out to be, upon closer inspection, a pair of lacey women’s underwear. Refusing to cow to Bullock’s teasing, Oswald had balled the underwear in his fist, his jaw tight as he tilted his nose slightly into the air. All the better to look down it at Bullock and his cohorts.

With a sneer, he turned and proceeded through the exit.

“What the—they’re not actually a gift, Cobblepot! Those are evidence!” Harvey yelled behind him.

Oswald had turned his head, smirking as Gabe stepped between his retreating back and the detective’s approach. “Finders keepers. Isn’t that the expression, detective? I’ll treasure them always,” he cheekily replied, eyes narrowed to slits.

***

It isn’t until Oswald is back in his car, headed toward the nightclub that he unclenches his fist. His first instinct is to toss the offending garment out the window into the nearest ditch, but something stays his hand. They’re…soft, but more than that there’s something odd about them. They’re square, which is weird, isn’t it? Oswald may not be exactly familiar with women’s underwear, but he helped his mother often enough with the laundry as a child that he remembers their shape.

As he spreads them out over the empty middle seat, Oswald observes that the waistline is indeed rather angular. Perhaps, he muses, they’re simply a cheap design, though the fabric feels expensive enough—soft and pliable against the pads of his fingertips. It’s then that he notices it, and he has to turn the panties over to get a better look at what appears to be a tear.

It isn’t.

There’s an extra bit of fabric jutting out from the front.

He gasps, eyes widening as he realizes what it’s for. Oswald has never seen men’s underwear in such a style, but there’s no way in hell these are for women not with… _that_ hanging there. It’s a lacey tube, clearly designed to hold a penis. He’d been able to keep his cool at the precinct, years of schooling his expression for the likes of Mooney, but this has heat creeping into his cheeks and blood rushing in his ears.

_Damn you, Bullock._

Suddenly, the joke makes far more sense, and his jaw tightens again at the memory of Bullock’s smug face. Oswald knows he should cast them into the garbage, but as they pull up to the club, he hastily pockets them instead.  It’s a return to chaos as he enters the club, and his thoughts are consumed with perfecting the place for its grand opening.

***

He doesn’t think of the panties again, until they appear inside a neatly wrapped paper bag, stapled to the side of his freshly pressed suit returned from the drycleaners. Alarmed, his eyes immediately fly to the open door of his suite, horrified that someone may have seen him upend them onto his desk and arrive at the wrong conclusions. There’s no one there, however, and a few moments of careful listening reveals no movement beyond his door, only the soft echoes of preparations for the night ahead coming from the club below.

Carefully, he pads to the door to close it and throws the lock. For a hair’s breadth, he considers securing the cleaner’s silence by slitting her throat, but Mother would be displeased if her favorite drycleaner turned up in a gutter. Besides, these types of secrets were what cleaning ladies excelled at, weren’t they?

The next few minutes are charged with the kind of trepidation one only experiences when considering something entirely foolish. Oswald vacillates between curiosity and shame, but ultimately, he can’t resist the temptation. His mother would be appalled, but Oswald is his own man now and he just…has to know.

One door between himself and discovery, however, is far too dangerous and he hastily makes his way to the bathroom, where he can shut and lock a second one. With a deep, resolute breath, he forces himself to undress as he normally would, carefully folding each garment and laying them in a tidy pile upon the expansive countertop. With trembling hands, he lifts the panties without meeting his own gaze in the mirror and carefully pulls them on.

He shivers as the lace gently disturbs the sparse hairs of his legs, a gentle caress against the twisted scarring of his right knee. His breath hitches when he takes the final plunge and tucks his own penis into its lacey pocket. It feels dirty. Indecent. Horribly lewd.

Most of all, it just feels inexplicably good.

The panties are a perfect fit, though it comes as no surprise. He wouldn’t have tried them on if he’d thought for a moment they wouldn’t fit. That truly _would_ have been foolish. Yet, fit they do, and well; so well, in fact, that he cannot stop himself from looking despite his earlier hesitance. He turns around to face the full body mirror that stands adjacent to the oversized, clawfoot bathtub, his gaze starting at his feet.

Oswald is no stranger to his own body, knows its flaws—his bared leg only the cherry upon a gangly, pale sundae. The panties feel so good, but his struggles with his appearance as a youth has made him a vain creature, and he fears they won’t _look_ half as well. When his eyes finally reach his upper thighs, he is shocked to discover that the transition from pale to black lace is nearly seamless.

More so, it’s attractive. His eyes drink in his hips next, the lines of the lace as it clings comfortably to his waist like a second skin. Oswald’s hands trace the fabric over his backside as he turns around to see his ass reflected as something shapely and appealing. Hastily, he nearly trips himself to take in the full picture, cock and all, and bites his lip at the result.

It looks good. _He_ looks good. His hands carefully trace the fabric where it hugs his thighs, trailing them up to his hips. Finally, his fears abated, Oswald tests the most curious aspect of the panties of all. Gently, he cups his own balls, rolling them against the fabric and has to bite back a groan, his cock filling against the tension of its lacey confines. The sensation is dizzying. He can’t breathe for how suddenly he becomes aroused by the feel of it.

“Fuck,” he swears through a whispered exhalation, eyes widening. He never swears. Rarer still, he can’t stop touching. It feels _so. Damn. Good._

Experimentally, he grips his own length in a loose fist and pulls. He’s barely touching the lace, but he feels every inch of the drag and his cock thrums eagerly with the intensity of his need. There’s the smallest pinching sensation at his tip as precum wets the thin fabric. He closes his eyes, the sight of himself—aroused and desperate—too damning to contemplate. Oswald turns back to the counter, his hand gripping the edge for support as he pulls again, his fist all the tighter and his groan echoes around him.

He shakes his head at his own reaction, but he can’t stop, can’t spare the time to worry about being overheard, so he just gives in. There’s lube in the drawers under the sink and he may have zero experience with touching other people in this way, but he is intimately familiar with giving himself pleasure. He keeps the panties mostly on but frees his cock for fear of chaffing. The fabric stretches in response, hugging his ass all the more tightly, making his blood run even hotter.

Oswald fists himself again, intending to chase his own pleasure quickly, but the idea pops into his head and he finds it too good to resist. He turns his head over his shoulder, so he can see the fabric stretched tight over his ass, and then he slowly pistons into his fist. His balls squeeze as he watches his cheeks clench as if he were fucking into a partner and then he’s gone. Oswald’s eyes are glued to the sight, his hips rocking of their own volition, cock pulsing as he tightens his fist and drops his jaw to pant through his climax.

He isn’t sure how he managed to remain standing over the sink, but he comes out of his orgasm-induced haze with goosebumps on his skin, and semen on his fingers. He cleans himself and the countertop perfunctorily, then eyes his discarded underwear from earlier before tucking his cock back into the lacey pocket of the panties.

Oswald wears them all through the night, making his rounds in the club while reveling in the thrill of surrounding himself with strangers and goons who have absolutely no idea what secrets lay just beneath the surface. He decides then, that one pair won’t be enough and resolves to figure out where to procure more.

It’s all the sweeter knowing the panties weren’t meant to be enjoyed, and Oswald can barely contain his smirk the next time he and Bullock cross paths.

“What the hell are you so happy about?” Bullock demands as they both wait for Jim to return from forensics.

Oswald smiles sweetly. “Oh, nothing you need trouble yourself over, detective. Just enjoying the motions of the day.”

 


	2. I Feel Pretty

**Summary for the Chapter:**

> Oswald finally gets his hands a catalogue and treats himself to a new present. This chapter's theme song is Love Myself by Haillie Seinfeld (sp?)

While Oswald does manage to find a few moments for leisure in the evenings through the coming weeks, his plans to track down additional panties is temporarily waylaid by his subversion of Gotham’s underworld hierarchy. His ascension to King of Gotham is bloody and rife with peril, but ultimately successful. He revels in his victory, so caught up in the marvel of his achievement—from umbrella boy to King at the age of 301—that he nearly misses his opportunity entirely.

There’s a little Polish diner Oswald likes to frequent not too far from the historical neighborhood of his new home. His mother enjoys their paczkis on Fat Tuesdays, and their cheese and chive perogies are to die for. They’re a hole in the wall, as far as atmosphere is concerned, a bubblegum machine in one corner of the foyer and racks of free, local publications in the other. It isn’t Fat Tuesday, but he is determined to have perogies for lunch and as he enters the restaurant, a new title on the rack catches his eye, and Oswald just… _has a hunch_.

He dismisses his guards under the guise of ordering them to secure his usual seat within the diner. He then waits for his moment, until they’re suitably distracted by a waitress, to swipe it from the shelf and tuck it within the inseam of his overcoat. He quickly moves inside and proceeds to his usual table with none the wiser.

Later, when Oswald is finally alone, he retrieves the title, _Frontiers 2,_ from his coat and flips through its pages until he finds what he’s looking for. There’s a sample catalogue alongside a subscription form that offers a full line of various adult novelties, including unisex pajamas and lingerie for both women and men. The selections in the sample catalogue are slim, but he manages to find one that catches his eye. He fills out his order, as well as the subscription form using one of his aliases and a PO Box, quick to drop it in the mail on his way to make rounds the next morning.

It doesn’t take long for his package to arrive, inconspicuously wrapped in nondescript brown paper, free of all logos or other telling information. Oswald is immensely pleased with the company’s discretion. Butch eyes the package curiously as they exit the Post Office before regarding Oswald, questioningly.

“Wha’s that, boss?”

Oswald smiles sharply, reproachful as he replies, “I don’t pay you to ask questions, Butch.” The false sweetness drips from his tongue, immediately putting his henchman on alert, Butch’s posture stiffening, but Oswald continues reassuringly. “Besides, the less you know the better.”

Butch loses all interest in the package after that with little more than a nod as he opens the car door for Oswald. Still, Butch’s simple question has caused a surging spike of adrenaline, and Oswald feels the slight tremor in his hands where he clutches the small brown box. Luckily, Butch is distracted with driving and it’s only the two of them, so Oswald has time to compose himself as they make the quick commute.

Oswald can’t articulate, even in his own mind, why the idea of discovery frightens him so thoroughly. He is the King of Gotham, after all, and while the nature of his new purchase is personal, it’s really only clothing and he shouldn’t feel ashamed. Yet, the idea of anyone knowing about these particular undergarments sends his heart racing in a panic.

He’d been taught at an early age the price for being different. He is older now, powerful in ways his childhood tormentors could scarcely conceive, and yet he knows that the world is largely unchanged. His new guilty pleasure could be used as a mechanism to cause his downfall, to undermine his newfound power. It shouldn’t be true, but it is.

 _No one can_ ever _know._

He lets the admission settle within his bones and resolutely accepts it. By the time they arrive home, Oswald is over the epiphany and ready to prepare for his meeting with Jim that evening. He happily clutches his package and barks his orders on his way through the main floor and up the stairs.

***

The new piece couldn’t have arrived on a better day. Oswald doesn’t have anywhere to be or anyone to threaten for the next few hours. In fact, he’d already been in high spirits at the prospect of wielding his new power over the self-righteous head of Jim Gordon. There was a time, not long ago, when he may have forgone the formalities and played a bit more humbly with the detective. No more. The idea of Jim sitting across from him, expression pinched with contrition, as he is finally made to put forth a little effort into this relationship has Oswald slightly breathless already.

He can’t help but wonder what Jim would think—

But no. He has waited for the moment where he might finally get to don a new piece of lingerie—this time of his own choosing—and he refuses to let the occasion be marred by Jim Gordon, of all people. Oswald is many things, but foolish isn’t one of them. He’d fantasized about the detective, early on, focusing on ways he could maneuver the man into his bed—each strategy more ridiculous than the next—before finally letting the notion go entirely. There is no circumstance or future in which Jim would ever deign to truly befriend Oswald, much less touch him in the ways he so profoundly desires.  

Neither is Oswald willing to submit to this base need by paying for a partner. Not only would it put his secrets in the hands of an untrusted stranger, but he doubts his ability to perform under those circumstances. There’s a connection between two people that Oswald is keenly aware of, though he has yet to experience it himself, which he knows would be missing. One which is based upon implicit trust and acceptance, neither of those something he can buy.

Not one to be deterred, Oswald casts the thoughts aside as he finally opens the box. He carefully spreads the new pieces over his bed, just as he does his suits in the mornings before heading to the shower. He’d ordered a two-piece set this time. The panties are completely unlike his first pair, with a bikini style cut so that they look even more like women's panties than the last pair. They’re a mix of light and dark material, pale sage silk and sheer black. It’s a partial thong, and Oswald thrills at the idea of trying them on.

With a contented sigh, he shifts his attention to the top. He’d wondered, almost immediately after his first experience, what it might feel like to cover more of himself in soft, delicate fabric. What it would be like to wear something over his nipples, that might rub against them during the day as a tease for pleasure soon to come in the evening. Oswald’s nipples had always been sensitive and, as he studies the tank top with its sheer black material running through the center of pale green silk, he notes that the seams will lay precisely over each one.

He shivers in anticipation, too excited now to bother with his discarded clothing beyond tossing each piece haphazardly to the opposite side of the bed. He picks up the panties first, curious as to how they will hold him securely without the special tube his other pair sports. While these don't seem designed specifically for men, the moment he pulls them on, it is clear his initial observations are erroneous.

The cut of the fabric is misleading in its appearance, but Oswald is certain that if he held this pair next to something from Victoria’s Secret of similar design and size, he would be able to denote additional fabric in the front and bottom. His balls are lovingly cradled by the silky fabric, his cock able to rest to either side with plenty of room.

When ordering this set, Oswald had dithered over the thong, but the material is surprisingly comfortable where it is wedged between his cheeks. The fabric is gentle as it rubs against his hole when he moves, the subtle motion more arousing than it has any right to be. Oswald barely manages to contain himself but is resolved to enjoy this set in its entirety which returns his gaze to the remaining article on the bed.

He eagerly reaches for the top and pulls it on. It feels very…effeminate. He thinks, fleetingly, of his mother, as he often unwillingly does during these times, and what she might say to him if she knew. Her acceptance and support of him is unwavering in all other known aspects of his life which are known to her, but Oswald cannot shake the parts of himself which are certain she would be disappointed in him for this especially, for all her prattling fears over non-existent hussies. One worry would only be replaced by another, if she knew.

Oswald shakes his head and clears his throat, his earlier excitement diminished somewhat at the errant thought, as usual. Nevertheless, he straightens his spine before approaching the full size, oval mirror that sits beside his armoire. He isn’t as fearful of looking as he was with his initial, unplanned foray into lingerie, but he steels himself before taking in the new piece. Again, he is pleasantly surprised by how well it suits his form.

The added tank top, with its pastel sage coloring brings out the green in his own eyes, contrasting them in ways that make the rest of his face more appealing.  The overall design is less racy temptation and more simple underwear, but the subtle accents—the tiny black bow atop a thin strip of lace at the center top of the tank, the thin straps of the shoulder, and its lighter color—all combine to make him seem softer somehow. Delicate. More approachable.

_Pretty._

He looks _pretty_. Oswald draws a shuddering breath at the realization, his eyes stinging as he feels euphoria wash over him. He slowly turns to observe the back of the ensemble and groans. The fabric forms a curvaceous shape above the globes of his ass, where they sit bared beneath the thin pastel elastic V of the thong where it disappears between his cheeks.

Oswald licks his lips, and swallows. On an impulse, he drags the mirror over to the foot of the bed, angling it slightly, and climbs onto the mattress. He spreads his legs as wide as comfortably possible and bends forward onto his elbows before glancing back at his reflection over his shoulder.

“Oh God…” he whispers shakily. He can see _everything._

He organizes his pillows into the center of the large bed and takes his time, tweaking each nipple when he resettles onto his back, bad knee straight out to recover from kneeling, and the left one bent and angled out. It’s more than just physical this time.

When Oswald touches himself, it’s with a reverence previously unexperienced. Oswald watches every movement, catalogues the way each tiny shift of fabric rubs against his skin in all of his most intimate places. Soon enough, he’s worked into a state that has him aching, cock standing straight up to peek out from beneath the waist of his panties.

He rolls his hips, enjoying the sight of the shaft fighting against the elastic, tip sliding over his abdomen seeking his attention. He throws his head back and groans lowly, breathing heavily through his nose to regain his composure. It wouldn’t take much to bring himself to completion, but Oswald resists. He treats himself nicely instead, hands slowly tracing the lines of his body.

He tests the limits of the tank, stretching it taut against his chest as he undulates to feel his nipples harden against the pull of the fabric. He slips a hand between his legs, pulls the thongs tight over his hole and nearly screams with how it tries to open in response—eager for the touch of some unnamed lover. He conjures a brief image of Jim, but just as quickly casts it aside. His mind excels at turning itself in circles, and he won’t be thwarted in this.

This is his, and his alone and Oswald can be content in that.

Clumsily, Oswald lubes his own fingers, spreading his left leg wider so he can better reach his entrance. He spears himself open on two, knowing his own limits so well, and curls the pads of his fingers up against his swollen prostate. For uncountable minutes, he fucks himself on his fingers while teasing his nipples. His cock drags against the fabric of his panties and it’s barely enough, but it _is_ enough.

He has but a moment to wrench the fabric of the tank to safety, stuffing it in his mouth to muffle his scream, before he’s coming, _hard._ Oswald is huffing with the exertion of his climax, his eyes rolled up into the back of his head while his body convulses with each pulse of his cock as he spends himself over his stomach.

 _“What the fuck…”_ Oswald whispers aloud, coming down from the aftermath. He is beside himself. Oswald is no stranger to self-pleasure, especially in recent months, but he has never come without the aid of his hand. Never.

That seals the deal, really.

When this business with Gordon is over tonight, Oswald is going to sit down with that catalogue and order himself an entire armoire full of lingerie. He’ll put a DNA-encoded lock on it if he has to, but he has to have more. Something for every day of the week.

Nighties for sleeping, robes for lounging, and things he can wear while handling business so that if he ever does get caught with his literal pants down, it could be overlooked as an eccentric taste for high-end, speedo-like briefs.

Oswald smiles to himself as he makes his way to the shower. He managed to avoid soiling the new set, and so sits it aside on the bathroom counter, planning to put it back on to wear under his clothes for the rest of the night.

He accepts that Jim will never willingly come to his bed in the same way that he accepts that the sky is blue. It is a simple fact of existence, but that knowledge does nothing to divert the giddiness of wearing his new lingerie in the man’s presence.  

So, when Jim is shown into his office that evening, the smile Oswald wears is entirely sincere as he asks, “Jim, old friend, what can I possibly do for you this very fine evening?”

**Notes for the Chapter:**

> 1: I am guessing Oswald's age at 30 when he throws Fish over that rooftop. Since we don't know his birthdate on Gotham, or I certainly don't recall its reveal, he tells his father after his mother has passed that he is 31. I'm assuming that between arkham and Galavan and all that and however long it took him to assemble his new base of operations he has at the beginning of season two that it's possible he has a birthday in there. Somewhere. I'd like to think he got to celebrate it with his mother one last time before everything went to shit, at least.
> 
> 2: Frontier was a LGBT magazine in Los Angeles from 1981-somewhere in the 2000s. I wanted to use one from before 2000 to kind of mimic the show in how it pulls from all time periods to create its own little realm. So...yeah. Anyway. 
> 
> The piece Oswald purchased in this chapter can be found here: https://shop.hommemystere.com/tiffany-camisole/
> 
> Just to forewarn, the next chapter is going to get a little less sexy and bit more angsty as Oswald confronts his love of lingerie, and how despite how good it makes him feel, whether or not he can ever share it with anyone, even if it does seem he's found someone to implicitly trust who also accepts him. You've been warned. <3


	3. Pieces of Oswald

**Notes for the Chapter:**

> This chapter is a two-for, and covers lingerie items 3 & 4\. Otherwise, this story would be seven chapters long, and I'm thinking the +1 chapter is going to be two parts or just exceedingly fucking long. I was fleshing it out yesterday and it just got sooooo out of hand, and then I realized that if I stretched this nygmobblepot thing into two chapters, like I was planning to do, then it gets a little redundant and the fourth chapter becomes super short, so this is the thing. I hope you like what i've done here with this one, as depressing as it gets by the end.

“Fortune favors the brave,” Oswald reminds himself of the words he’d spoken to Olga that morning. He’s never been indecisive like this, and the fear he feels is a new kind of terror. He eyes the items he’s laid out on the bed, a nervous fist pressed against the tight line of his mouth.

Oswald thinks about the events which had led him here, to this very moment, pondering the likelihood that Ed will reciprocate his feelings. Oswald has been through a lot over the past year, from King of Gotham to rock bottom and now he’s the mayor, living in the home his father left for him. A safe place that no one can take from him, with secret walls and hidden spaces, which help Oswald better guard his own.

Oswald can scarcely believe his fortune, for all the loss he’s suffered along the way to finding it. He’s been rather lucky, all things considered. A sharp wit will only get you so far, the rest is opportunity and timing—two variables often impossible to predict.

Which brings him back to the items on the bed. For the first time, Oswald purchased something based on what someone else might think of it. On the left, is a very modest purple and black, pen-stripe vest with matching boxer briefs, both of them very soft and some combination of spandex and rayon, Oswald is sure. He didn’t bother to read the description in its entirety. He’d seen it, and immediately thought of Ed. Of course, he hadn’t acknowledged at the time why he would do such a thing but now there seems to be some possibility that…

Oswald shakes the train of thought from his mind before he once again ties himself into knots over his chosen course of action. What happens after he confesses to Ed is out of his hands. It will either be met with welcome reciprocity or kind rejection. Ed would be kind, Oswald is sure. Though he is doing his level best to eliminate the prospect of rejection all the same.

Olga is working tirelessly to ensure that dinner tonight is perfect, and Oswald has carefully selected his outerwear; a black jacket over a less formal pressed white shirt with a smart, but vibrant red paisley cravat. He will look sophisticated, but casual. And quite fetching, if he does say so himself. He’s meticulously planned and prepared for this evening from start to finish.

This impasse he is currently presented with is just another added measure of preparation for an outcome that is uncertain. With that in mind, he eyes the second piece laid out before him. It is also a two-piece set, with a tank top and bikini panties, black satin beneath black lace over the front, and only lace over the back of each piece. There aren’t any frilly accents, just the lace and straight lines. It’s modest in a way, but far less conservative than the other piece in terms of design and function.

Oswald prefers the black. It’s prettier, and less purple. It’s more honest. The problem is, Ed might see it, and it will be less easy to pass this article off as expensive men’s underwear. Whereas, with the other piece, Oswald can still experience the thrill of showing without the fear of disrupting any potential intimacy.

He eyes the black number longingly, but his hand strays toward the purple. It’s a nice set, he knows, it just isn’t his usual taste. Oswald rolls his eyes at himself. There’s no guarantee either of these will even be seen. Ed could outright reject him tonight, and then all this time wasted pondering the philosophical question of ‘to be or not to be,’ for God’s sake.

He snatches up the purple set and casts off his bathrobe. If—and that is a BIG if—things end up with Oswald in his underwear tonight, testing the water is the most logical option. Oswald loves the way he looks and feels in his personal collection of lingerie, but as with the rest of his tastes, there is a good possibility that _any_ potential romantic partner will not understand or worse, be offended.

Finally resolved, Oswald goes about donning the more conservative piece. Which, he reminds himself, he did pick with Ed in mind. He’s doing the sensible thing, and the notion fills him with renewed confidence. It’s one less thing to worry about, at least, and he does like how the material feels. Though, he avoids looking in the mirror before putting on his suit. He’s already tried it on, and it doesn’t look bad; though it certainly is nowhere near his most attractive piece. It’s a set for showing, but not showing off.

“It’s good enough,” he chides himself. “Baby steps.”

Without a backward glance, Oswald retires to the dining room, where Olga has begun to set out dinner. He takes in the place settings on the table, the feast that’s laid out and the roaring fire. Joy radiates outward from his chest, suffusing his entire body with a warmth that is evident in his eyes where his face is dimly reflected near the bottom edge of his father’s framed picture. Perhaps it is the overwhelming emotion within Oswald himself that colors his perception, but his father’s portrait looks proud.

Everything is going to be perfect.

***

Ed doesn’t show. Oswald waits, and waits. The food is long cold by the time Ed calls, informing Oswald that he met someone, and he’ll explain when he sees him tomorrow.

_Met Someone._

The words haunt Oswald all through the evening as he attempts to exhaust himself before bed. Perhaps Ed met someone that could help them advance their plans for the city. Or, perhaps he’s met someone he believes is a threat to Oswald or himself and is following up to ensure their swift demise. Or, Oswald begrudgingly considers as he remembers the tone of Ed’s voice over the phone—excited and hurried—perhaps he’s met _someone_.

Oswald grinds his teeth. How typical that Oswald would find the love of his life, and before he can amass the courage required to seize it, some distraction presents itself. Still, he forces himself to remain calm, a distraction may only be a distraction.

Temporary, Oswald muses with a sigh.

A passing fancy.

Certainly, whoever this ‘someone’ is, they can’t offer Ed the kind of all-encompassing acceptance that Oswald can. Ed murdered his last ‘someone’ and while Oswald is perfectly understanding of Ed’s actions toward Ms. Kringle, no other well-to-do ‘someone’ could possibly claim the same. That is, of course, assuming this person _is_ well-to-do. Which is a thought that brings with it an entirely new bag of worries.

Oswald is resigned, once again, to holding onto his feelings for just a little while longer. He makes his way up the stairs to his room and prepares himself for bed. As he’s folding his dirty clothes, readying them to be sent out to the cleaners, he catches his reflection in the mirror. He’d forgotten all about his earlier dithering, and now he takes the moment he previously avoided to look himself over.

He approaches the mirror with a pronounced limp, his leg exhausted from the day's errands, tracing his appearance from head to toe with a frown. It had been foolish to be so presumptuous, and more so to choose something that does nothing to flatter his features. He may as well have just worn plain underclothes, with how unappealing he feels wearing this horrid purple monstrosity. Angrily, Oswald yanks the vest over his head, shucking the shorts immediately after.

He marches to the chest of drawers against the far wall, where he’d hastily stashed the black lacy number he originally decided against. He’d been in a rush when he’d shoved it into his sock drawer, no time to put it away properly. Ed was supposed to have been arriving soon. So much for that. Oswald digs the garment out from under his socks and pulls it on. He treads back to the mirror and—

“Much better,” he tells his reflection.

Where the purple and black pin-stripes had distracted from his eyes, the black makes them pop. Too, the purple vest had made his shoulders seem broad, and sharp and the shorts used a soft cup to obscure the shape of his cock. The straps of the black tank top, however, produce the exact opposite effect. His shoulders and collar appear more delicate, more inviting. And the panties show off his thighs, the shape of his genitalia is subtly visible and dare he think it: enticing.

It is much more appealing than the piece he’d selected to placate another person’s sensibilities. And who could predict the desires of others anyway? Oswald guards his secret affinity for lingerie more closely than most people guard their own children. Surely no one could guess what the Mayor of Gotham frequently wore beneath his bespoke suits.

Tonight’s events are the misfortune that comes from cowardice, he decides as he again remembers his words to Olga. Oswald hadn’t been brave earlier and now he is disappointed with himself. What is the point of half-measures? If Ed hadn’t become distracted, if he’d made it to their dinner and Oswald had managed not to choke on his confession as he had all throughout the day, would they have ended up in here? Would Ed have taken Oswald to bed?

And would Oswald have felt desirable in those shorts? In that vest?

What a fool he was.

All for the sake of modesty.

Oswald takes himself to bed instead, but his thoughts are too jumbled and chaotic to do much more than bask in the comfort of satin and lace against his skin. Oswald resolves that once this distraction of Edward’s has run its course, he will not make the same mistake.

 

***

It isn’t a passing fancy.

Oswald tries to comfort himself with new purchases. His lingerie collection is larger than it’s ever been, but he doesn’t find the same joy in it as he once did. It stays locked away in its secret room inside the manor.

He is certain, that once he finds a way to make Edward love him in return—once he has someone to appreciate him in his finery—that Oswald will feel good wearing it again.

***

Ed isn’t gentle in his rejection. In hindsight, Oswald knows he mis-stepped with Isabella, as hauntingly similar to Ms. Kringle as she was and as certain as Oswald is that she was likely one of Dr. Strange’s experiments, his bold move was naught but an overplayed hand. Oswald realizes, as Ed shoots him in the chest and tosses his love aside with a sneer, that he has mis-stepped in many things.

***

Oswald survives, but his confidence is shattered. Ed doesn’t love him. Gabe has betrayed him and confessed that his men view him as nothing more than a _freak_. Oswald doesn’t like that word; he never has. It’s a term that followed him as a child and continues to do so as an adult, despite his many successes.

Oswald cannot help but think of his secret room just then, sitting full of his most personal things back at the manor. Had Ed found it? Did he laugh about it with his pathetic ring of followers?

Does He call Oswald freak?

His eyes water, lump forming in his throat. When he returns to Gotham to exact his revenge, the first order of business will be to burn the lot.

It pains him to think that his mother was wrong.

Love is nothing to run toward, and Oswald finds that he was happier without it.

**Notes for the Chapter:**

> Oswald's pieces are here: https://shop.hommemystere.com/products/PinStripe-Vest.html
> 
> and here: https://xdress.com/collections/back-in-stock-mens-panties/products/secret-satin-camisole?variant=28474840387
> 
> If you're liking the story so far, a little kudo goes a long way! Thanks for reading! <3


	4. Reclaim

**Summary for the Chapter:**

> Jim guest stars. LOL. But probably not in the way you’re hoping for... yet.

**Notes for the Chapter:**

> Little disclaimer: All opinions expressed in this fic about other characters belong to this iteration of Oswald Cobblepot, not the author lol
> 
> I’m really not trying to bash anyone, but let’s be real—most of us are not particularly kind to either our exes or our competition or other people who piss us off lol and neither is my Oswald.
> 
> Also, Oswald is not having the time of his life in this chapter and he is swearing a bit more which seems to be something he does more often on the show now too which I can totally relate to.

Oswald makes good on his plans. He returns to Gotham with Ivy, dedicated to enacting his revenge. He finds very few moments of solitude as he plans and organizes, but he does manage to investigate his secret room and it appears to have been undisturbed in his absence. He bags up each piece, refusing to linger too long on any one item. He knows if he lets himself linger, his resolve will waiver.

These things…they are not supposed to be enjoyed the way Oswald enjoys them. Alone. As often as he thinks of secretly wearing one, the idea no longer holds the same appeal. They’re meant to be shared, and the simple truth is that there will never be anyone to share it with. He clenches his teeth as he tosses the bags into a dumpster, a few alleys away from the Syrens, and sets the whole thing ablaze.

Oswald hates Ed anew as he watches it all burn. It’s his fault that Oswald can no longer find joy in this one small thing. He can feel regret welling up inside of himself, but he stubbornly pushes it down and marches away. He buries the longing for those nights he found comfort in lace and silk in a tiny little box, and then shoves it into a corner of his mind right next to his love for Ed. He will cut it out of himself, piece by piece, and he will never let himself feel this way again.

***

He rises and falls, again, and Oswald is beginning to fear that his life follows a rather disturbing pattern. One minute, he’s on top the world with a brand new club and more power than he’s ever had even as the mayor, and the next he is clinging to Jim Gordon—why is it always Jim Goddamned Gordon witnessing all of Oswald’s lowest lows—shaking in fear of Ed’s ghoulish visage. And in front of the press too.

Of course, despite all his best machinations, things only go from bad to worse and he’s back in Arkham being tortured by a madman. This accursed city has no shortage of men like Jerome, many of which Oswald has gleefully employed from time to time, yet he terrifies Oswald in ways he’d rather not consider. Oswald is keen to play along if it might restore him to some power, but all too soon he realizes that Jerome’s only masterplan is chaos. Oswald has no time for anarchists, even less for anarchists with no intention of paying up.

A world without order is a dream of men without vision. The institution of justice is a maze of red tape, one which has bound Oswald as often as it has lifted him up. It’s an intricate game of chess, and Oswald may not always win but he only plays with the best. Fish, the Falcones, Ed…hell, even Jim when he’s willing to play dirty (more and more frequently, it would seem, Oswald thinks with a chuckle), those are the kind of players with which he will happily engage. Worthy opponents.

Oswald just can’t align with Jerome’s greater vision. There’s no tangible benefit. Who wants to live in a world of penniless equals? Not to mention the man’s unpredictable penchant for violence. Oswald can appreciate the need for a good stabbing, but he at least first establishes a need. Call him a sadist, but Oswald has always wielded those ‘dark urges’ as his father had called them, with purpose.

He goes to Jim. They don’t always see eye to eye, but Oswald knows that if anyone can stop Jerome, it’s the headstrong detective. He might be romanticizing the man a little—old habits do die hard and Jim always cuts a striking figure in his pre-made, fitted suits. Jim could wear a trash bag and Oswald would still want him. Though, he’s long given up on even the fantasy of Jim Gordon viewing him with anything other than disgust or as someone barely tolerable to look upon.

It is what it is. And right now, what it is, is damned desperate.

The evidence room is dusty and, frankly, a little unnerving, and Jim is suitably irritated as he finally opens the door. As if Oswald isn’t trying to do the right thing here. Mostly. Jerome has eyes all over the city, and Oswald is risking much to try and help Jim bring him down. He could at least be a little more grateful for the assistance.

“Well, this is a first,” Jim says.

Oswald barely resists the urge to roll his eyes. “Are you doing anything about Jerome?”

“We’re looking for him!” Jim is defensive. “Do you know where he is?”

Ha! As if Oswald would tell him if he did. GCPD running in half-cocked, guns blazing like cattle to a slaughter. Oswald’s slaughter. No thanks. He tells Jim as much, which only serves to make the man more irritable. Honestly, as if this is fun for either of them.

“Why did you come here if you’re not going to help me?” Jim fairly growls the question in his face. If circumstances were different, Oswald would stab him somewhere non-fatal and leave him on the floor. Probably.

As it is, Oswald is terrified, and his next words are honest, if _unhelpful_. “He scares the living hell out of me, okay?”

And maybe Oswald doesn’t have much information, but he’s trying to establish himself as a plant. If Jim will just trust him, maybe they can help each other when the real shit begins to hit the fans. Besides, just seeing Jim’s face and his determination gives Oswald some measure of comfort. Oswald vows to later analyze the odds that so many of his lowest moments should be witnessed by a man who shudders to spend more than ten minutes in a room with him.

Of course, it wouldn’t be Jim if that comfort wasn’t accompanied by vexation. The man keeps asking him the same damn questions, as if Oswald didn’t just tell him five seconds ago that he doesn’t know where the hell Jerome is. Honestly! There’s no time to ensure Jim’s cooperation should Oswald supply him with information once he finally knows what his own role is supposed to be in Jerome’s scheme to gas the city. They’re interrupted, suddenly, and Oswald trusts precisely zero other people. He makes haste out of the room, trusting that Jim will listen when it’s important.

***

Oswald manages to save the whole damned city, and Jim is no help at all!

 _“The city of Gotham thanks you!”_ Oswald recounts the words with a sneer.

The cheek!

He’s been stuck on this ridiculous, wannabe Hindenburg for hours! The next time he sees Jim Gordon, Oswald is going to gut the bastard where he stands and toss him over the blasted pier.

Probably.

***

Goddamn Jerome Valeska to all nine circles of Hell.

He and Butch are squatting in the Falcone mansion, twiddling their thumbs while that psychopath’s brother continues to bring the chaos. How does one plan under this kind of pressure? Oswald shakes his head. He needs to find the calm in the midst of this storm.

He eyes Butch as the man chomps down all the fried chicken. This would be easier if Oswald could get some brain food over here, but no. Butch has decided to be petty. Oswald would shoot him if he weren’t so useful. Besides, he does want to help Butch. He knows how it feels to be looked upon as a freak. Still, Oswald has long since given up trying to hide his own freak flag, pretty much from the moment he publicly displayed Ed as a permanent ice sculpture. Well, semi-permanent as it turned out.

Butch just needs to find the silver lining, is the point, Oswald thinks as they drag their cargo down the street. Super strength, for one—there, Oswald has found it for him.

Besides, there’s no way he didn’t enjoy stuffing that idiot’s nose full of chicken bones just as much as Oswald enjoyed watching him do it.

***

Oswald doesn’t manage to shake Butch until after he’s given over his intel on Dr. Strange’s whereabouts and agreed to participate in the man’s abduction. He skulks off into the night, taking an obscure route to circle his destination long enough to detect any signs of a tail. It’s been a long day.

A long week.

A long thirty-three years.

Finally, a few hours later, Oswald is as certain as he can be that no one has followed him. Butch probably assumed he would head back to Falcone’s, but Oswald is clever and, more importantly, has no wish for unwanted company before he deigns it necessary. Oswald needs a shower, food and some peace and goddamned quiet.

There is a safe house, one he kept under an alias no one yet knows about.

Did Oswald lie about being completely without resources? Yes.

Does he feel bad about it?

He looks around the empty apartment, richly furnished with plush chairs, fireplace and a kitchen routinely stocked by a one-person staff who has never met her employer.

No. He doesn’t feel guilty in the least, he decides, smiling gleefully as he takes it in with a breath of relief.

_Finally._

Clapping his hands together, Oswald makes for his first order of business. A nice, hot bath in a ridiculously huge tub. He makes a quick detour to the kitchen, snagging a protein bar from the pantry and tearing into it on his way to the bathroom. Once there, he digs through the drawers, appreciating the manner in which the place has been kept all these long years. Once he finds his way back to power in Gotham, Oswald will give Estelle a hefty bonus for taking such good care of his things.

He finds eucalyptus and sandalwood bath oils in the drawers, Epsom salt under the counter and a stack of plush, over-sized towels in the cupboard by the door. Oswald leaves his clothes in a pile on the floor, too exhausted to care one way or the other. When he’s settled into the tub, the aches of the last few weeks—especially that of his bad knee—find reprieve in the near-scalding water.

With no one around making demands, or otherwise trying to torture him into submission, Oswald is able to reflect on the events of the past few days. He spares a moment for his brief reunion with Ed, and the subsequent betrayal. He rolls his eyes at Ed’s parting words.

“…you come against Lee, you come against me.”

“Tsk.” Oswald snorts derisively. “Idiot.” He cannot fathom what it is about Lee Thomkins that gets men all in a twist. First, and more than probably still, Jim, and now, Ed.

“Man-eater,” he declares with a giggle.

Poor Jim, he never stood a chance.

And Ed, well. Oswald sighs as he lowers himself further into the tub. “Ed is an idiot.”

Lee will chew him up and spit him out when she gets whatever it is she’s using him to accomplish. For all that Ed declared Oswald a free man after his mother died—all that talk about how love makes men like them weak—he sure is susceptible to just about anything with legs under a skirt.

“Hypocrite.”

Oswald frowns suddenly. What did he ever see in Edward Nygma? With time and distance, Oswald feels as if he sees the man clearly for the first time since their initial meeting at the GCPD. Ed was there for him in a time of personal crisis, when Oswald truly hadn’t cared if he lived or died, but in hindsight…it wasn’t altruistic at all. Ed needed something— _someone_ —to validate him; to help him _become._

Killing Ms. Kringle and getting away with it would never have been enough. He had looked to Oswald to groom him into The Riddler.

Oswald has never needed that. His entire adulthood has been spent pulling himself up by his own bootstraps. He plots his own course. Oswald took the name given him to spite him and made it his own. He is the Penguin because he chose to embrace it proudly. Fighting it, he found, was simply a hurdle to his own success. Ed doesn’t have that kind of confidence, which is why he seeks others to build it for him. In truth, Oswald pities him.

But he doesn’t love him. He thinks, maybe, Ed was right about one thing. Maybe Oswald never did, certainly not at the time when Oswald believed it most.

It’s another sort of pain that washes away in the bath water and leaves him feeling lighter as he climbs out and wraps up in a towel.

He treads into the bedroom far more relaxed than he’s been in months. He opens the top drawer of the dresser to find some fresh underwear and then gasps.

He’d forgotten about these.

When he’d been indulging himself as mayor, Oswald had ordered a few items of lingerie under the alias holding this safe house with instructions to Estelle to put them away. They aren’t even the really sexy kind. This safe house was organized around Oswald’s idea of comfort. It was always meant to be a place he could come to when all other doors were closed to him. For only the direst of times.

He’d ordered these items with comfort in mind. Oswald stopped his subscription to his catalogues the same day he’d burnt his entire collection. Now, his pulse thrums as his fingers slide over the soft material of the panties before him. He knows if he opens the second drawer, he’ll find the corresponding nightie. In the closet, the robe will be hanging there.

There are few things he regrets in recent months more than burning his lingerie in a fit of pique over a bad breakup. A breakup for a relationship that didn’t even exist, no less. He had labeled Ed a hypocrite in the tub, but Oswald is the greatest hypocrite of them all.

He’d been ready to tell Butch to embrace his new oddities earlier and here, not so long-ago, Oswald had tried to burn one of his own away. He frowns at that thought.

_Is it an oddity?_

Implementing gnarled chicken bones as a torture device is probably odd.

What are a few pieces of racy underwear in comparison to that? 

_‘If he wants to wear leather, he should just wear leather…’_

He’d said that, hadn’t he? True, he’d been talking somewhat facetiously about Galavan, but he _had_ said it. Moreover, he’d meant it.

Why all the double standards in application to himself, then? Oswald pulls the panties from the drawer, then gathers the matching nightie from the next. He carries them over to the bed and sits himself down on the edge, ignoring the way his towel pulls awkwardly at his waist.

Why fight something he enjoys to such a high degree? Especially something so harmless. Burning his collection was rash, but ultimately a good thing considering everything that’s happened since then. That, and the fact that his father’s home is currently seized with the rest of his assets. He is going to have to work on that, going forward.

Oswald smiles slightly to himself. There’s nothing wrong with wanting a little something that is just for him. If sexy underwear were only meant to be worn with a partner, then they’d sell them exclusively in pairs for couples. Sharing is a choice, and Oswald must allow himself to admit that deciding to share with Ed, whether it had all gone differently or not, was the wrong decision.

He bans all further reminiscing over that particular slip of sanity for the remainder of the evening. Tonight, is a night for relaxation, he decides. Jeremiah Valeska is still at large, Butch and Tabitha have ensnared him in their plot against Dr. Strange, and Oswald is currently sitting in his end-of-the-world luxury apartment in the sky. The city can go to hell for the rest of night as far as he is concerned.

With a good book and something more filling than a protein bar in mind, Oswald casually slips into the panties before donning the nightie. He spares a few moments in front of the mirror to admire his appearance. It’s a thigh-high gown with a pink and purple floral pattern. He can’t seem to stop smiling as he rubs his hand up and down his sides, luxuriating in the feel of it against his palms. He’s missed this very much.

Remembering the robe in the closet, he retrieves it hastily and pulls it on as well. It’s pink satin, the same shade as the roses on the nightie. Yes, the whole outfit is rather delicate, and Oswald finds it’s exactly the right expression for the situation he’s found himself in lately. His situation as a free man, at current, is tenuous at best and easily reversed if he is not careful, but once again he resolves not to think of it for now.

It’s liberating, Oswald discovers, walking around the apartment in his silky new pajamas free as a…well, free as a penguin. He laughs to himself, a light unrestrained chuckle as he grabs a book off the shelf— _Huckleberry Finn_ —and lounges, sprawled, over the chaise set before the gas fireplace. Oswald had turned it on earlier before throwing together a more substantial dinner in the kitchen.

He settles in with his book, quickly losing himself to the antics of young Mr. Finn. _’You don’t know about me without you have read a book by the name of The Adventures of Tom Sawyer; but that ain’t no matter...’_

***

He’s not sure how much time has passed, but he suddenly feels as if there are eyes watching him and the bottom of his stomach drops out.

  _Please, God, don’t be Butch._

It isn’t Butch.

It is infinitely worse.

Oswald looks up toward the entry way, heart completely seized where it used to beat in his chest, at the sight of a haggard Jim Gordon staring back at him, as wide-eyed and slack jawed as Oswald himself must be.

And the night had been going so well, too.  

**Notes for the Chapter:**

> This is the mini-dress: https://shop.hommemystere.com/natasha-mini-dress/
> 
> This is Oswald's robe:https://bodyaware.com/collections/mens-satin-underwear/products/sexy-robe-for-men?variant=12110279311427
> 
> PS I kind of feel like a huge doiche because this is a cliffhanger of sorts and I can’t get back to it until Monday, please don’t kill me!!!


	5. The One Time...

**Summary for the Chapter:**

> Confrontation ensues. Otherwise know as, Oswald panics and Jim ponders his own feelings and how to fix what he accidentally broke. Things don’t exactly go according to plan. Lol Sorry for the delay, the archive was being all broke-ass again.

**Notes for the Chapter:**

> The piece in this one is the red one at this link. You will need to scroll down to get to it.
> 
> https://bellatory.com/clothing/Sensual-Nylon-Nightgowns---Feminine-Sleepwear-For-Men

For long seconds, there is absolute silence as this moment is written between them in time. Every instinct that Oswald possesses is screaming at him to run, to avoid this situation even as it is happening. He doesn’t. Moving now would only display more of what Oswald does not want seen, least of all by the man before him. He is infinitely grateful for what little his thigh-length robe covers and that, at the very least, it is not his scarred leg which is visible from the entry. Though, given the way Jim’s eyes keep shifting and narrowing, cataloguing Oswald’s appearance as if he can’t quite believe it is real, Oswald doubts his knee would even register Jim’s attention.

Irritation wars with his nerves— _Jim knows. Jim’s seen!—_ Oswald clears his throat and channels that irritation, primly saying, “While I am curious as to how you managed to unearth this particular safe house, your explanation can wait until after you’ve had a shower.” Oswald boldly returns Jim’s gaze with a hostile edge. “Not to be rude, but you look like hell, James, and I can smell you from here. The bathroom is that way.” He gestures down the hall and forces himself to return his attention to his book though he sure as hell can’t discern any words, let alone, any meaning from its pages.

He hears the audible click of Jim’s teeth as he finally snaps out of his stupor. Oswald spies him in his peripheral, shuffling toward the hall somewhat awkwardly as if in a daze. He waits for the tell-tale sound of the bathroom door closing before he is up and out of his chair. Oswald shuffles to his room then, finally letting himself retreat for some much needed, albeit speedy, deliberation.

He needs to contemplate his next move, but as soon as he’s thrown the lock on the door, Oswald is falling back against it, mind swirling with panic. His secret is no longer his alone. He’s been caught, and not just by anyone. Jim Gordon had seen him.

Jim had seen.

 _Jim_ knows.

Fuck.

“Fuck, fuck, fuck, fuck,” Oswald whispers the oath over and over as he tries to regulate his breathing. 

If Oswald ever had an edge over the detective, rare as it is, any future advantage is well and truly lost now. He is trying, desperately, to imagine how it could be worse and falls entirely short. He has equivalent, or worse, personal dirt on all of his criminal rivals but he has nothing new on Jim Gordon. There’s no advantage, or information, that either them hasn’t already expended in the past. Oswald can’t even threaten a loved one, because Jim is a depressing loner these days!

He briefly imagines busting down that bathroom door and violently ensuring the man’s silence but…he doesn’t _want_ to kill Jim. Can’t stomach the idea of seeing him dead because, goddamn it all, he still has mixed feelings about the man. It’s foolish for hope to have lingered so long without an ounce of encouragement and yet, in the innermost depths of his being, Oswald continues to pine. He’s made peace with wanting and never having long ago, but now.

Now, Jim’s seen him at his most vulnerable, and it scares him so thoroughly that Jerome couldn’t hope to compete. This feeling of utter hopelessness isn’t new, but Oswald has felt it rarely enough in his life that it catches him unguarded. _What to do…what to do…_

Change, first, obviously.

Unable to think beyond that first step, Oswald makes his way to the dresser. He catches his reflection as he walks past and pauses. He doesn’t turn to look at himself, eyes firmly on his feet but after a few breaths he turns toward the mirror fully. Finds his own stricken gaze staring back at him, and it shocks him into squaring his jaw and shoulders. With a studious eye, he appraises his own appearance.

He wants to understand _how_ Jim may have seen him, so he tries to imagine it from the man’s perception. He puts aside the notion that the outfit is out of the ordinary for a man and focuses instead on the whole. The lighter colors compliment his pale skin and dark hair, making his eyes pop. The robe is soft and softens, in turn, the curves of Oswald’s shoulders and neck. It falls to his thighs, where the panties remain hidden from view. At least, he consoles himself, Jim hadn’t seen _everything._

And the view, Oswald decides, isn’t all that bad, aside from his knee which wasn’t visible to Jim anyway. Maybe it’s arrogance, but Oswald likes how he looks and he is not going to apologize for it. The fabric and design are flattering, and if Jim has anything to say about it, Oswald will plainly tell him to go to hell.

Still, he should change. Jim may have already seen—cat’s out of the bag on that point—but Oswald’s stomach still twists into knots at the thought of letting him see it again. He might be more comfortable with himself now than he’s ever been, but he is by no means interested in sharing. Especially with someone he knows wouldn’t be interested, much as Oswald wishes—

No. That path only leads to madness and heartache.

Oswald gives up trying to determine Jim’s reaction, and continues to his dresser. He pulls on a pair of black silk pajama bottoms—it’s gone two in the morning, propriety can go hang—and swaps the robe for a matching long-sleeve button up. He leaves the panties on—why not?—and makes his way back out into the main room of the apartment.

When Jim joins him a few minutes later, cleaner but dressed in the same clothes as earlier but with tie and jacked folded over his arm, his eyes take in Oswald’s appearance for the barest of moments before finding something near the fireplace to casually stare at instead. There’s a light bloom of color on the detective’s cheeks, but the man says nothing for which Oswald is infinitely grateful.

It’s never been his style to let things lie, however, so Oswald plainly says, “I know I don’t have to tell you, but just so we’re clear, my underwear is absolutely no business of yours. That said, why don’t you tell me what the hell you’re doing here. For that matter, how you even know where ‘here’ is.” 

Jim exhales like he’s been holding it for hours, his shoulders sagging before he falls into the nearest chair—a small settee across from the chaise Oswald had been reclining in earlier—like a puppet cut free of its strings. Oswald resumes his seat opposite the detective on the edge of the chaise, expectant.

Finally, Jim says, “Last time we raided the Iceberg Lounge, I kept coming across the same name, mostly by chance until I noticed a pattern. I didn’t submit it to evidence, thought it might be handy, but I don’t know. I’ve had a hell of a week. Jeremiah is still out there, and he knows I’m still alive. I figured…it’s probably not a great idea to be at home right now. I remembered the address. Thought it was worth a shot.” He pauses to rub a hand over his mouth and chin, a nervous habit of Jim’s that Oswald recognizes, before continuing. “I thought it’d be empty, if it was here at all.”

Oswald hums, accepting the explanation as honest. Jim looks too tired to think up such an elaborate lie on the spot. He’s not a very good actor, besides. “I suppose I won’t throw you out.” Jim raises his eyebrows at that, but Oswald continues accusingly, “ _If_ you can resist arresting me the second my back is turned.”

Jim looks infinitely relieved as he nods. “It may surprise you to hear it, but I’ve actually got bigger concerns than recent Arkham escapees.”

Oswald allows himself to smile at that. “Fair enough. Though, I suspect you will want my assistance saving our fair city once again.”

Jim frowns. “And I suppose you’ve already decided on a price?” his eyes momentarily flash with something angry. “Let me guess: a full pardon from the mayor?”

Oswald arches an eyebrow.

“Your friend, Nygma,” he pauses, jaw working before continuing, “and Lee, had a similar request. Except, their plans were more along the lines of holding the city hostage until pardoned in exchange for me and a map I found to Jeremiah’s bombs.”

Oswald huffs, then tilts his head considering. “Be that as it may, neither of them diverted a giant gas bomb from deploying over the city or called Harvey with a tip about the time frame of Jeremiah’s ultimate plan to demolish half the city.”

Jim’s eyes widen at that last bit of intel, and Oswald allows his smile to widen in response as he leans forward. “You’re welcome.”

Jim surprises Oswald, then. Instead of arguing or demanding he offer his assistance altruistically, Jim laughs. The smile he gives Oswald next is bemused. “Fine. And don’t think for a second that I don’t know your reasons were entirely selfish, but I _am_ actually grateful. Too grateful to care, at any rate.”

“And you’ll make sure the mayor is equally grateful?” Oswald presses, forcing Jim to sober slightly.

Jim’s expression is entirely sincere, his eyes intense with a promise forthcoming. “I’ll speak to him on your behalf.”

“I’ll focus my resources to your cause, sparse as they may be presently.”

Jim nods, and Oswald lets that be the end of it. He is confident that Jim’s word on this is true, and it’s nearing three-thirty already. “You can take the room across from mine if you intend to get any sleep.” Oswald stands and makes toward the hallway and he can feel Jim’s eyes following him from the room. He looks back over his shoulder, catching the detective’s gaze, as he says, “Good night, Jim.”

Jim blushes scarlet, no doubt still embarrassed by what he’d witnessed earlier, but manages a gruff, “’Night, Oswald,” in return all the same.

When morning comes, and they begin to plan their move against Jeremiah, the awkward air from the night before has dissipated entirely. Oswald crosses his fingers that Jim has elected to forget it, though some discontent part of his heart rebels at the idea. Jim had been stricken with shock at the sight of Oswald in his lingerie, but he hadn’t reacted with outward disgust either.

Oswald shakes his head. Dwelling on the nuances of Jim’s reaction is little more than grasping for straws. The man had been relieved when Oswald dismissed the possibility of discussing the awkward encounter and hadn’t brought it up since. That didn’t mean Jim had forgotten it, however, and Oswald would do well to remember that fact. Their allegiance would be short-lived, only lasting long enough to eliminate the current biggest threat to Gotham; Oswald knows this.

It would be unwise to underestimate the consequences of Jim’s newfound knowledge. He could easily use Oswald’s secret to bring him to heel in the future. He could make Oswald his slave, if he so chose.

He eyes Jim to see the man bent over the map they’d used to find Jeremiah’s bombs, assessing it for any clues as to where the man might be hiding now. Oswald can’t look for too long, however. Watching the detective in his element is akin to staring at the sun, and Oswald’s world is shrouded in darkness where Jim doesn’t want to dwell. He is an impossible dream, and Oswald knows that having been found in his lingerie has only made that dream all the more impossible. It shouldn’t hurt to lose something one has never had, but it does hurt. It’s likely Jim has always thought of Oswald as a freak, but on the slim chance he hadn’t, now there is no doubt that he will.

Regardless, Oswald likes working with Jim again, though being in his presence for so long is beginning to unearth some familiar, long-buried feelings. It’s clear that Jim is still a good man, but Gotham has begun to take its toll. It’s evident in the pinch between Jim’s eyebrows, the tight square of his shoulders as he broods and the diminished laugh lines around his eyes and mouth—as if all the joy has been slowly syphoned out of him. It tugs at something within Oswald, makes him want to comfort Jim and give him something to be happy about.

But Jim will never want those things from Oswald, and no matter how much time passes or how deeply he buries those feelings, they just won’t leave. Oswald isn’t able to explain it; doesn’t fully understand how Jim managed to lodge himself so thoroughly beneath his skin. At first, Oswald can admit, it was simply an infatuation with an idea of a person— _a friend_ —he created around Jim’s image. Yet, as time passed, Jim continued his crusade and no matter how far he is made to bend in order to keep fighting for this city, the man doesn’t break. Oswald can’t help but admire that quality, that kind of unerring tenacity, though it often puts them at odds.

It’s fruitless, and foolish. But Oswald still wants Jim to want him, despite knowing the futility of wishing. He wants Jim to see him, and like what he sees. It makes Oswald war within himself over his own impossible feelings. It’s distracting, and it’s for the best to keep the man as much at arm’s length as possible. Oswald cannot afford to misstep again, least of all with Jim. At least, until he can come up with something of his own to hold over the detective’s head.

 

\---

 

Jim’s drumming his fingers over the top of his desk, willing himself to focus on the reports before him but he can’t stop thinking about it. It’s been weeks since he and Oswald started working together on untangling the Valeska brothers’ webs within the city’s underbelly. They work well together, and Jim can concede that they always do when the need arises, but this time is different. Nothing is riding on secrecy or the exchange of favors as the mayor already pardoned Oswald for his transgressions leading up to his last stay in Arkham.

Jim isn’t blind. He knows that when Oswald isn’t working with him to follow a lead on their shared endeavor, the man is steadily climbing the rungs of the underworld, one felony at a time. But Jim doesn’t have evidence, and it’s not his case right now besides, so he ignores it in favor of their new status quo.

That isn’t what’s bothering him.

When they’d begun this new alliance, Jim had expected Oswald to take advantage of the access and proximity that came with it. Instead, Oswald is more distant he has ever been. He greets Jim with practiced courtesy, exchanges information perfunctorily and then disappears entirely until there’s something new to share.

It’s unsettling, but not because the source of Oswald’s behavior is a mystery.

Jim knows the reason for it, and instead of being happy to have the upper hand for once, all it does is piss him off. Does Oswald think Jim’s so narrow-minded that he can’t cope with a little risqué underwear? Has Jim fallen so far in Oswald’s eyes, that he’s just another dirty cop, willing to use whatever means necessary to press an advantage?

Jim can’t deny that he’s wished for Oswald’s easy cooperation in the past, when the chips were down, and Jim was at loose ends with an important case, but this makes him feel dirty. Watching Oswald hold himself in tight posture as they exchange awkward pleasantries before getting to work. The way Oswald’s smiles are held rigidly in place, quick to acquiesce to Jim’s demands. Not because he wants to, because Jim can see the corners of his eyes tighten whenever he asks for something that will cost Oswald personally. Jim doesn’t do it on purpose. He doesn’t have a beat on the current status of Oswald’s working relationships in the underworld, but Oswald never says no. Never argues.

It’s like he’s just waiting for the other shoe to drop and taking every measure to ensure that he doesn’t force Jim’s hand. It’s the same kind of behavior you see in battered wives, and Oswald might be a criminal, but Jim doesn’t want that kind of resentment. If Oswald is going to resent him, he wants to earn it on his own merits, not based on some fear Jim has no intention of validating.

He just wishes there were a way to clear the air with Oswald without earning himself a knife in the spleen. He supposes the direct approach is what most people would take, but how do you go about telling a hardened mobster that his lingerie kink is neutral territory? That you have no intention of using it against him? As if Oswald would believe it.

Jim gritted his teeth. Why couldn’t he just…not care? God, how did it even come to this? It’s the last thing he’d expected that night when he’d decided to use the safe house he’d unearthed. Oswald must have a dozen of the damned things; how did they end up at the same one?

He can remember it as though staring at a photograph. Oswald hadn’t noticed him right away, and Jim had stood in the doorway trying to process what he was seeing. He’d never seen the gangster so relaxed, his head in a book, hair down and body lax with ease as he slowly turned the pages. The soft pastel pink of Oswald’s robe had gleamed in the firelight—must have been satin or silk, Jim muses—and done little to cover the majority of Oswald’s bare, pale leg.

It should have looked incongruous. A guy with Oswald’s dark hair and build should have thin legs with wiry black hair to match. Instead, Oswald’s legs could have been shaved for how smooth they appeared and sparsely haired. His kneecap wasn’t overly pronounced, and his thighs and calves weren’t feminine, but their definition leaned more toward curvy than cut.

Overall, the look suited Oswald surprisingly well, and he’d been somewhat disappointed that the man had changed by the time he’d exited the shower. Jim had wondered, at the time, if Oswald had changed entirely or simply thrown pajamas on over it all. Jim could feel the blood rushing to his face once again at the thought. He can admit that he’s always acknowledged, in passing, that Oswald is attractive. Most people with dark hair and bright eyes are pleasing to look at, for Jim at any rate. He’s definitely caught himself looking more than once. Especially when Oswald was running for Mayor and the guy was literally everywhere.

But Oswald is a criminal, a murderer, and so whenever he catches himself looking a little too closely, he’s quick to redirect.

But now. The damage is done.

It can’t be unseen.

The barrier between Jim’s attraction and his professionalism has been well and truly compromised. Every fantasy that’s ever threatened Jim’s peace in the past few years now haunts him throughout the day until he is powerless to give in and let himself imagine it. How things could have been different between them.

Sometimes, it’s all Jim can see.

It’s driving him slowly up a wall.

Rubbing his temples, Jim manages to get his mind back on his paperwork. It isn’t until Harvey slaps him on the shoulder that Jim realizes he’s zoned out again.

“You’re still working on that? It’s been three hours, buddy.”

Jim groans. “Is it six-thirty yet?”

Harvey chuckles. “Look, I don’t know what you did. I don’t know who you did it to, but you need to take care of it. You’re useless when you’re like this.”

Jim sighs. “I don’t even know where to start.”

Harvey shrugs. “Good old-fashioned groveling tends to work wonders. For me, anyway. A few drinks, a couple’a nice gifts…water under the bridge.”

Jim furrows his brow. That might not be a bad idea, actually. Jim doubts Harvey would give the same advice if he knew Jim was worrying over Oswald, so he doesn’t mention it when he agrees, “You know…you might just be a genius, Harvey.”

“Nah.” Harvey grins. “You’re just that big of an idiot. I’ll cover for you. Go take care of…whatever it is. Details later. Especially if you fuck it up.”

“You got it,” Jim lies, feeling his headache subside as an idea takes shape. He’ll offer half-truths to Harvey later, but he thinks it’s best if his partner remains mostly in the dark on this one.

***

Jim is feeling better about the entire situation a week later, when he presents his peace offering to Oswald at their scheduled meeting. They’re inside the study at Oswald’s inherited mansion, recently returned to its owner as a result of the mayor’s pardon. Jim is sure he’s nailed it right up until the moment Oswald opens the package.

The customary polite smile drops from Oswald’s thin lips, but it isn’t replaced with an actual smile. No, Oswald is staring at Jim like he’s set fire to his mother’s grave. He tosses the gown—it’s a deep red ankle-length nightie, with a satin skirt and lace bodice—onto the desk between them. Jim stares at the gown, wondering what Oswald doesn’t like about it, until finally Oswald snaps him out of his confusion with an accusation.

“Is this your idea of a joke, James?” Oswald’s nostrils flare with outrage as he stands, looming over Jim from the other side of the desk. “Because if it is, I must say, your delivery lacks finesse.”

Ah, crap.

Jim finds himself standing in return to vehemently reply, “It’s a not a joke, Oswald!”

The words don’t deliver the kind of reassurance Jim was hoping for. They came out all wrong, angry at the accusation. In response, all the emotion leaks out of Oswald’s face, the fire in his eyes suddenly cold as ice, as he squares his shoulders and tightens his jaw. “Are you threatening me?”

Jim is still gaping, trying to think of some way to salvage his horrible attempt at an apology. Oswald seems to take his silence as answer enough.

Jim watches in abject panic as Oswald’s façade seems to wilt around the edges. His eyes are wide with betrayal, on the verge of outright tears from the very thought of Jim hurting him in this way. When he speaks, it makes Jim's heart seize up into his throat, because he’s never heard Oswald sound so defeated.

“I don’t understand,” Oswald despondently intones, then angrily adds, “I’ve done everything you wanted, Jim!”

Goddamn it. Why couldn’t he just let it go? Oswald is a criminal, capable of all manner of heinous shit, and doesn’t deserve comfort least of all from Jim, who he’s tried to manipulate at every turn since the word go. Jim rounds the desk and gives it to him anyway. He grips Oswald by the shoulder with one hand, snatches up the gown in the other and shoves it at Oswald’s chest.

“It’s not a damn joke, Oswald, and it sure as hell isn’t a threat!”

And this is definitely not how Jim envisioned this going. He figured Oswald would put the gift aside, open it later and read the note Jim had painstakingly written in order to apologize and promise to never tell a single living soul what he accidently discovered in the safe house that night. Instead, here he is yelling inelegantly, because when he gets put on defensive, that’s his default setting.

“I know I can be a fucking prick sometimes,” he goes on, fairly hissing his words, “but I’m not a complete asshole, okay?”

Oswald is staring at him, but at least it isn’t with that haunting look of heartbroken betrayal. This one is more...confused curiosity. Jim swallows a growl, because sometimes Oswald can be so fucking frustrating and of course he has to make Jim do all the work. He’s supposed to be clever, should have been able to put the pieces together in their proper fucking order without Jim having to make a complete ass of himself.

If either of them get out of this with their dignity intact, it’ll be a fucking miracle.

“I wasn’t ever gonna say anything about it, but you’re different now.”

Oswald squints as if to balk at Jim’s accusation, but Jim cuts him off. He’s on a roll now, damn it all. “You walk on egg shells around me, like I’m gonna pull a megaphone out of thin air and announce it to the world that Oswald Cobblepot likes pretty little nighties, if you don’t say or do exactly what I want. And maybe there are plenty of people in this city who get off on having that kind of power over someone—present company included—but I’m not one of them, and it pisses me off that you’d think I’d actually do it.”

Oswald’s face is redder than a tomato, mouth quivering with upset, by the time Jim finishes his tirade, and it takes the wind right out of his sails. He huffs a defeated sigh as he loosens his grip on Oswald’s shoulder, letting his hand fall so that he can un-ball the gown he’d been clutching in the other. He holds it up against Oswald’s front, his own face feeling warm.

He can't bear the deer-in-headlights expression on Oswald's face, so Jim drops his gaze to the floor. “It’d be a nice color on you,” he manages to admit bashfully.

Christ, it’s like he’s thirteen again, telling Becky Daniels that her braces make her face look shiny. He’d meant it as a compliment. She’d slapped him so hard it made his head swim. He never says the right thing.

He’s rescued from his self-flagellation when Oswald squeezes the air out of his lungs with a fierce embrace. Jim would make light of it, say something along the lines of _‘it’s not that big a deal, Oswald, really’_ but the choked sob against his chest that follows kills the notion entirely. Oswald may be a criminal, but he's shaking apart and it's all Jim's own damned fault.

So, he rides it out. Wraps his arms around the other man so he can run one up and down Oswald’s back, soothing. He doesn’t know what to say, as usual, except...

“It’s alright.”


	6. Friends In the Dark

**Summary for the Chapter:**

> Hoo boy. Here you go, my dears. Finally, we get to the climax of the story. Ah, ha, ahah ahahah ha. Shut up, it's a solid pun. 
> 
> Anyway, this is the final chapter of this short, but sweet ride. After much deliberation, however, I have decided that this is probably going to become a series. I have too many ideas for future fics based around my iteration of Jim and Oswald navigating their relationship, not to mention their own feelings. ugh, there's just much fun to be had. So, I've gone ahead a created a series for this. Subscribe to that if you want to read more from this universe. 
> 
> Thank you all so much, by the way, for your kind words and encouragement throughout. It really means a lot.

**Notes for the Chapter:**

> Oswald's panties as later described in the chapter: https://www.lingeriediva.com/collections/mens-lingerie/products/white-stretch-lace-wonder-bikini?variant=7568893181982
> 
> A closer look at the red gown featured in this chapter and chapter 5: https://www.herroom.com/shadowline-31737-silhouette-53-inch-gown.shtml

Oswald loosens his hold on Jim in increments, but he can’t bring himself to let go entirely. It feels safe here, where Jim is warm and holding him back, hands rubbing along his spine, and Oswald needs this so badly he could weep all over again. No one but his mother has ever touched him so kindly, and Oswald is loath to end it. He is horribly embarrassed and hiding his face against Jim’s shoulder means he doesn’t have to see the man's pitying expression.

“Why is it always you?” Oswald asks, his voice rough and breath hitching from sobs he shamefully couldn’t withhold, though he’s managed to calm somewhat. “Always when I’m at my worst.”

He feels Jim’s quiet chuckle against his cheek, hears it rumble low against his ear where it is pressed against the detective’s collar. “This is hardly you at your worst, Oswald.”

Oswald stiffens a bit at that. Of course, Jim is only here because Oswald has been pathetic these past few weeks. He’s only being nice and as much as Oswald is enjoying this, Jim must be so uncomfortable. He tries to pull away, but Jim’s arms tighten around him.

“Hey, come on. Don’t be like that,” Jim admonishes gently. “I just meant that I know who you are, I know things you’ve done…what you’re capable of, but this?” Jim opens their embrace slightly, keeping one arm around Oswald’s back while the other pulls the gown out from where it had gotten trapped between them. “This is no bad thing, Oswald.”

Oswald sighs. He is having a hard time forming words, so unexpected is this situation. He wants badly to question Jim’s kindness, find some flaw in his claim or some ulterior motive but more than anything he just doesn’t want to move. Instead, he asks, “Wherever did you find a full-length gown? None of my catalogues ever had any.”

Jim gives him an encouraging squeeze. “Ever heard of Excalibur’s?”

A laugh is startled out of him. “No, but it sounds dreadful.”

“It is a little. Me and Harvey worked a case a while back, it’s on the outskirts of the city, near the northern burbs. Anyway, one of our witnesses worked there. They only sell lingerie, but they have a lot of stuff that’s just for men or unisex...” He indicates the red nightie. “Like this one.”

“Jim…” Oswald can’t let it go, he has to ask, before Jim comes to his senses and pushes Oswald out of his arms. “I know you aren’t cruel, not really—unless you have to be, but I don’t understand why you’re being so kind about this.” Quieter, he adds, “To me.”

“Honestly?” Jim huffs. “I figured you’d stab me if I brought it up in conversation. I didn’t think you’d open it in front of me. I wrote you a letter.”

“That’s not what I asked, Jim Gordon.”

“Kind to you, I know.” Jim does end their embrace then, but he doesn’t go far; shifts just enough so he can meet Oswald’s eyes. “That night, at the safe house, you looked…”

Jim is looking at him so intensely, searching for the right words, that Oswald can’t help but supply a few for him, “Uncouth? Ridiculous?”

The little pinch between the detective’s eyebrows is back as he regards Oswald with incredulity. “What? No.” Jim licks his lips. “ _Happy_. You looked happy. And I messed that up for you, didn’t I? I just…it’s one thing when you’re scheming and looking for trouble, trying to get ahead and I can’t tell if you’re being sincere or trying to manipulate me, but for a second there…I just saw you. And I guess—I guess I wanted to see you again.”

Oswald sucks in a breath. He can’t possibly be saying...

Part of Oswald wants to pick Jim’s words apart immediately, get to the heart of Jim’s meaning but he doesn’t think the man knows all the answers himself. Instead, Oswald thinks back to all his fretting over Ed and the perilous road to which cowardice had led him.

Boldly, he asks, “Do you want me to try it on?”

Color washes up Jim’s neck, right to his cheeks, his mouth opens on a tiny gut-punched exhalation and his eyes widen just a fraction to let Oswald know he’s been caught off guard by the offer. Oswald simply raises an eyebrow, and Jim is tense, swallowing thickly.

“Try it on?” Jim repeats, tone stupefied. “Now?”

Oswald shrugs, feeling a little embarrassed the more he thinks about it. He may have misread. Seen something in Jim’s words and actions that wasn’t intended, and he can feel panic trying to wrest control. He forces a tiny smile, despite his inner turmoil. “Just…if you want. I don’t have anywhere to be for a while.”

Jim is staring at him, utterly silent and Oswald begins to babble, trying to rescind the offer in a way that is dignified, and failing completely. “Of course, I realize you must have other things to do. You probably need to get back to the precinct, after all. I don’t keep normal hours, as you know, so you’ll have to excuse my thoughtlessness. We didn’t even exchange information, did we? Tabitha and Butch are planning to move on Strange in the next few days, you should stay clear of the narrows, Jim, and don’t get in their way. Also—”

“Please.” Jim finally says, blinking as he shakes his head. It’s like his mind had been sucked out of his ears and then forcefully dropped back into his skull. “Yes. Try it on.”

“I—” Oswald sucks in a gust of air, face feeling hotter than the sun as he nods distractedly and reaches for the gown. Jim is still holding onto it, but he hands it over easily.

The detective makes to follow Oswald out of the room, then hesitates. “Do you want me to—er, should I wait here?”

Oswald feels his lips twitch at Jim’s display of absolute befuddlement. He can scarcely believe he’s about to model something for someone else, let alone Jim Gordon. An eager Jim Gordon, at that. _Is this the twilight zone?_

That thought actually gives him pause.

“Not to dither, but you haven’t recently had any run-ins with Tetch or Scarecrow, have you? Or a…a pod person?” Jim looks pained at the line of questioning, as if Oswald has twisted a knife he didn’t know was protruding from Jim’s innards. “Not to say that I don’t appreciate you’re being here or the very fine gown…it’s just…normally you don’t want.” Oswald is annoyed with himself. He’s asking questions he doesn’t want answers to but can’t seem to stop, and now Jim is probably going to leave. He decides he may as well just say it. “I know I disgust you, normally. You can’t stand to be in the same room with me, so I just have to ask. I don’t want this if you’re not really yourself at the moment.”

Jim’s smile is as self-deprecating as his words. “Really am kind of a bastard, aren’t I?”

“No,” Oswald denies. “No, I’m…I once told my father that I wasn’t a good man.” He looks at Jim, eyes watering because he _wants_ _this_ so badly, but he would rather stop now than have Jim emerge from whatever bubble they’ve cast themselves into and regret everything. “I’m not a good man, Jim. Whatever you’ve said or done to me—I know I deserved it. I just want you to know, that while I appreciate this lovely gift, you don’t have to do anything else. Or say anything else. You can go. And we can just forget this ever happened.”

“Just like that, huh?” Jim asks, taking a breath. He moves toward Oswald then, advancing until he’s got Oswald’s back against the wall.

It’s a familiar position, one that makes him incredibly nervous. Oswald manages to stutter out a reply. “Promise. I won’t ever tell, Jim.”

Jim raises his hands to Oswald’s face, and he can’t stop the tiniest of flinches before they come to gently rest against his neck and jaw. That pained expression is back on Jim’s face as he says, “I don’t want to forget it.” He rests his forehead against Oswald’s, so close that Oswald can feel his breath on his face. “Do you remember telling me that it was better to walk with a friend in the dark, than to walk alone in the light?”

Oswald swallows thickly, because he does remember. And he remembers Jim’s ultimate rejection, as expected as it had been. He nods. “Yes—”

“I can’t pretend that I’m okay with your methods, and I know there are things about you that will never change, and I accept that. Thing this is, this city…it’s changed _me._ I don’t know if it’s for the better or worse, but I can’t go on the way I once did. I can’t pretend that I haven’t had to get my own hands dirty to force the kind of change that’s necessary and I can’t lie to myself and say that I wouldn’t do it again.

“We’re at odds in terms of tactic, but I don’t think our purposes are all that different, Oswald. When push comes to shove, we each do what we have to. You’re the only other person I know that cares as much as I do about this city. And maybe you’re not altruistic or noble, but if I have to navigate the city in the night, then you’re the person I want walking beside me.”

Oswald is already breathless, but Jim kisses him, then, and he is completely lost. He feels lips moving against his own for the first time, and he knows there’s something he’s supposed to do, but he can’t think with how little air he’s able to draw through his nose and how loudly his pulse thumps in his ears. All he can do is stand frozen in panic, like a cold, stiff fish. He’s mortified, but his mind’s suspension of disbelief can’t seem to engage.

Too soon, Jim is backing away. He eyes Oswald speculatively for a moment, then says, somewhat disbelievingly, “Oswald…have you never…was that your first…?”

Oswald feels shame begin to creep up, shocking him out of paralysis, and quickly diverts his eyes to Jim’s rumpled tie. “Don’t make fun,” he quietly demands.

Jim doesn’t say anything. Instead, he lowers his lips to the spot just beneath Oswald’s ear. He can feel the man’s smile against his skin and all of the air leaves his lungs in a rush. His hands spring to action of their own accord, clinging to Jim in a bodily plea to _do that again._ Jim gets the message, teeth joining his tongue to short-circuit Oswald’s thoughts entirely. Nothing exists outside this moment. No shame, no fear.

Just Jim’s lips, and teeth, and tongue; his hands caressing Oswald’s face, and his whispered words against his ears. “Just open your mouth for me, Oz, and do what I do.”

_Oz._

Jim has given him a nickname. That alone is enough to startle a moan from his breast, and Jim spares no time in taking advantage. This time, when Jim kisses him, Oswald is pliant. He sucks Oswald’s bottom lip between his own, licks gently before releasing, only to seal their mouths together entirely. Oswald’s tongue seems to instinctively respond to Jim’s, rising up to meet the intrusion with enthusiasm.

Jim moans into his mouth, and Oswald goes boneless against the wall as Jim presses even closer. In answer, his body reacts for him, hips arching up to meet the thigh Jim pushes between his legs. It’s inelegant, and he’s sure they look ridiculous, certain his fumbling impresses no one, but Oswald can’t bring himself to care. Not with the way Jim seems to revel in it, driving Oswald’s own desire up and up.

With a reluctant groan, Jim forces some distance between them. His eyes are dark with want—want for _Oswald—_ as he mostly pants his demand, “Let’s go put that gown on.”

Oswald nods soundlessly, unsure if his legs will make it, as coltish as they feel beneath him. It’s like he’s walking through molasses as he leads Jim down the hall from the study to his own room. Jim takes a seat on the edge of the four-poster bed, pulling off his suit jacket as Oswald makes for the bathroom.

Once enclosed within its safe confines, Oswald pulls off his own jacket, shoves it into his mouth and soundlessly screams into the fabric. This is real. This is happening. Oswald cannot think of anything else as he sheds his cufflinks, shoes, suit and socks. Everything but his panties, which are a sheer, white lace bikini cut. They cup his sack nicely, though Oswald has to adjust his now half-hard cock so that it just barely peeks over the waist band.

_Jesus Christ._

He’s really going to go through with it. When Oswald had tried on that first pair, he’d firmly believed that it was a secret he could never share. Later, he’d nearly made a huge mistake and broken that rule for Ed. Even though Oswald had somehow knew Ed would find it odd, choosing conservatively to suit the man’s tastes.  

Oswald carefully pulls the vibrant red gown over his head and smooths it over his body. It’s beautiful, and Oswald isn’t sure how many emotional highs and lows he can endure in this one afternoon, but he is speechless with it as he takes in his appearance. The gown is sleeveless, with a V-neck bodice comprised of a floral lace pattern over satin material, which is soft against his skin.

The deep V cuts low into the masculine cleft between his pectorals and meets with a tiny red satin bow in the center. There are cups in the breast, but they’re removable. Oswald finds that when he takes them out, and readjusts the bodice, it fits perfectly to his own shape. Truly designed, as Jim had said, for either sex.

The bodice meets with a small bit of elastic around the waist to join it with the skirt. Oswald thrills at the length. The skirt is a silky material—nylon or satin—which is Oswald’s favorite to sleep in. It swishes around his legs in flowing waves as he moves from side to side to test its sway. It’s easily the most feminine thing he’s ever worn, and Oswald adores it.  

Jim was right: The color suits him well. Oswald usually only uses red as an accent color, but he finds this gown’s bold shade makes him look exotic. He certainly feels desirable in it. Oswald never thought he’d be willing to share this secret with anyone after things went so abysmally with Ed, but Jim had chosen this with _Oswald_ in mind. He is far more confident in the results of modeling this for Jim than he was when entertaining the idea for Ed.

Oswald forces the name Ed out of his mind.

“Fuck Ed,” he whispers, defiantly, hoping his mother isn’t haunting a corner and listening in. Lord knows what she would make of this, but even that thought doesn’t bring him down.

Jim is waiting on the other side of the door, because he _wants_ to see Oswald in the gown he chose especially. He _wants_ Oswald, and it’s all he can do to reign in his own excitement. Jim isn’t talented with flowery words and riddles, but he says what he means. He won’t blind himself to Oswald’s sins, doesn’t waste time with false pretenses. It’s not absolution he’s offering.

But it’s an acceptance Oswald never dared hope to gain from anyone, let alone Jim Gordon.

Oswald has his hand on the doorknob when it hits him.

“It’s always been Jim.”

This could end badly.

_‘…when you find it, run to it…’_

***

Jim looks up when Oswald re-enters the bedroom, his eyes full of awe as they slowly appraise him. “Jesus Christ.”

Oswald sniggers. “Not in this house.”

Jim’s laugh is an airy, light thing that Oswald didn’t know the man was capable of producing.

He does a half turn, not wanting to limp in a circle, and asks, “What do you think?”

Jim’s eyes are bright with mischief as he replies, “I think I need a closer look.” He gets up and Oswald can’t describe it as anything less than prowling, the way Jim tilts his head and circles him. Without warning, Jim’s sweeps him from behind with one arm against his back and another behind his knees. He hoists Oswald up into a bridal carry and marches them toward the bed. He knew the man was strong, but this is ridiculous.

Oswald has Jim’s shirt clutched in his hands, mouth open in shocked surprise. He never would have imagined Jim to be so charmingly playful. He lets loose a very unmanly squeal when he is unceremoniously tossed onto the bed, Jim crawling up after so that he is braced above Oswald on his hands and knees.

Oswald giggles, embarrassingly, yet unable to hide his happiness at this unfathomable new side of the detective. “Oh, my God.”

“Just Jim,” the man tosses back wickedly, with a wink, before he moves back into a kneel. All the better to run his hands down Oswald’s sides, tracing the shape of the gown all the way down to his hips, where they are bracketed by Jim’s knees.

“Did I tell you that you look gorgeous?” Jim asks.  

Oswald can’t speak. He shakes his head instead, his face hot with how affected he is by Jim’s hands and words.

“You look stunning.” Jim leans in again, kisses Oswald sweetly on the lips, once, twice, before trailing kisses along his jaw and down his neck, all the way to the tiny little bow in the center of Oswald’s chest.

Oswald’s hands are in Jim’s hair before he consciously decides to put them there. He’s always wanted to touch it, wondered how it would feel between his fingers. Would it be as soft as it looked or brittle with product? To his absolute delight, Jim’s hair is the former. Soft and malleable, flitting through his fingers like silk. How on earth does he keep it in place during the day? Pomade?

What an odd thought to have, Oswald muses, with Jim’s mouth against his throat. He giggles again, drunk on the moment, and Jim looks up at him questioningly.

Oswald shakes his head. “Don’t stop,” he pleads.

Jim lowers himself fully onto Oswald then, like a heavy, wonderful blanket, his hands coming to frame his face. “I won’t,” he promises. “But if I do something you don’t like, tell me, okay?”

Oswald nods. He doubts there’s anything he wouldn’t let Jim do to him in this moment, and perhaps that’s the point of Jim’s edict. Feeling bolder by the minute, Oswald takes a moment to raise his hands to Jim’s face. He wants to always remember this and, being gifted with near eidetic memory he can, given enough physical detail. He can take a picture of Jim, just as he is right now.

He trails fingertips over Jim’s forehead, runs his thumbs down along his temples until they reach the soft arch of his cheekbones, then skirts them over his blunt nose, soft lips and strong jaw. Jim's expression is one of relaxed curiosity as he watches Oswald explore him.

“What are you doing?” he asks, finally, with a lopsided grin.

Oswald meets his eyes. “Remembering you.”

Jim’s expression shifts, then, to something between realization and fondness. “You’re something else,” he whispers between them.

Oswald grins. “Shut up and touch me, Jim. Don’t you think I’ve waited long enough?”

Jim’s eyes dance with mischief at Oswald’s demand. He leans up on one elbow, trailing his other hand over Oswald’s chest. His thumb slips beneath the lacy bodice to draw circles around his nipple. Oswald inhales sharply, only serving to encourage. “Where should I touch you, Oz? Here?”

He groans at the use of the hypocorism. Jim’s endearment. Oswald is fairly certain it is not normal to be so turned on by the employment of a simple nickname. But this is something from a man he never considered would deign to call him friend, let alone address him as one. And they aren’t really friends, now, are they? This thing between them—this thing Oswald has never been able to name—it’s this.

_This._

They are not friends.

Oswald is delirious with whatever they actually are to each other. Opening his mouth to say, “More, Jim. Please, please touch me. I want you to touch me everywhere. I want you to…”

Jim kisses him, groaning against Oswald’s mouth as his touch morphs from playful caressing to heady intent. They grip the skirt of Oswald’s gown and hastily yank it up, so that his legs are bared, and Oswald has a brief moment of panic, because his knee is hideous, and Jim won’t like it.

Yet before he can utter a word of these doubts, Jim is sliding down his body, until his mouth is hot and wet against the juncture where Oswald's thigh meets his groin. He can feel Jim's breath breeze through the lace of his panties and his cock aches at the proximity. Oswald slides his hands over Jim’s shoulders, meeting with stiff fabric rather than skin, and whines, pulling at it impatiently. “Off, off, _off_.”

“Yeah,” Jim agrees, hastily kneeling to peel himself out of his button up, casting it aside before untucking his undershirt from his pants and hauling it over his head as well. Oswald looks his fill, noting every curve, freckle, mole and scar before meeting Jim’s eyes.

“You are devastatingly handsome, James Gordon.”

Jim huffs a laugh, tucking his chin bashfully before he puts a hand on his belt. He shoots Oswald a look, issues a dare. “More?”

Oswald decides to call his bluff and raises his arms, folds them behind his head and grins. “By all means, Detective, do make haste.”

“Lend me a hand?” Jim asks, beckoning Oswald up with a finger.

Oswald rolls his eyes. “Helpless,” he complains, sitting up. Jim is still kneeling over his legs, and the shift brings them into an interesting position where Jim’s chest is level with Oswald’s eyes. He has a sudden desire to taste, and he’s moving forward without thinking, to take one of Jim’s nipples into his mouth. His arms come up to brace Jim from behind as he pulls him closer.

Jim’s answering moan sounds as if it is dragged out of him, and Oswald makes a mental note regarding Jim and sensitive nipples. Jim’s hands are in his hair then, pulling Oswald’s head closer in a silent bid for more. Oswald delivers, goes with his gut, and gently pinches the nub between his teeth. He then trails his lips down Jim’s chest, encouraged by the needy sounds Jim is making, until he encounters the belt.

He chances a final, questioning glance up at Jim to which he gets a breathy, “Yeah.”

Oswald makes quick work of it. Unfastening the belt, popping the button and zipper. He helps Jim kick them off entirely, underwear and all, until Jim is kneeling over him completely nude. The contrast between Jim’s pretty, tan skin and the deep red of Oswald’s gown proves too much of a distraction to resist. Oswald takes the end of the skirt and rubs it over Jim’s thigh.

Jim sucks in a breath. “What…” Then groans as Oswald does it again, just beneath the heavy sack of his testicles.

And what fine testicles they are, Oswald muses. They’re covered in soft, light brown curls that climb toward the shaft in a downy mound. Oswald is lost to his exploration, uncaring of his own inexperience as he takes Jim in hand. His cock is slightly longer than Oswald’s, but about the same girth. He’s circumcised, where Oswald is not, head flushed with arousal. Oswald takes it into his mouth and hears Jim’s surprised, “Ah!” as the man practically folds in around him.

He can feel Jim trembling with need, wanting to drive into Oswald’s mouth. He admires the man's restraint, pulls off and finds Jim’s gaze.

“You can,” he says. “I’d let you.”

Jim’s eyes are wild, before he swallows thickly. “Not your first time, Oswald.” He softens the tiny rebuke with a slow kiss.

It’s different from the others. His tongue moves in and out of Oswald’s mouth in an imitation of what Oswald wants most, lips gently caressing his own in concert. Oswald sighs and falls back, taking Jim with him. He feels Jim’s hands move up his thighs until his fingers find the waist of his panties. He pulls them down just enough to free Oswald from their confines.

“Like this,” Jim utters against his mouth. He fits their bodies together and grinds down into Oswald, their cocks brushing together.

“Mmmph,” Oswald moans at the contact, then breaks their kiss to reach into his night stand. He retrieves a vial of lubricant and hands it off to Jim.

The man smirks down at him. “I like the way you think,” he says, pressing a quick peck to Oswald’s forehead before squeezing a bit onto his fingers. He then tosses the bottle aside, but close enough if they need more, before taking them both in hand.

“Here.” Jim guides Oswald’s hand to join his own. Once he’s got them both encircled, Jim kisses him again and proceeds to rock his hips. His cock slides back and forth through their joined hands, slipping against Oswald’s cock, and suddenly he gets it. He clutches Jim’s hip with his free hand, then pushes up to meet Jim’s downward thrusts.

Jim rewards him with a groan and punched out, “That’s right, baby, just like that.”

“ _Fuck_ ,” is Oswald’s elegant reply. It all feels so good, and he can’t cope with Jim’s praise, his ridiculous pet names. The way he kisses Oswald, like he’s something to be savored. The way his body moves against his own, all sensuous motion and deliberate provocation.

“ _Jim…_ ”

Whatever is in his voice, Jim interprets it correctly, tightening his hand just slightly. “Come on, Oz, let me see…let me see you come. So fucking pretty...”

“Ah!” Oswald is powerless to stop at that. His body seizes, head thrown back and hips stuttering as all focus is lost to the intensity of his climax.

“Fuck!” He hears Jim rasp above him, warmth coating his stomach. He forces his eyes open, so he can see Jim take his pleasure in turn.

The man is stunning.

Oswald can scarcely believe this is real, but it _is_ Jim panting through his orgasm above him, mouth slightly open and eyes squeezed shut. His bangs have fallen forward, completely disheveled and Oswald loves him as he has never loved anything or anyone.

He always has done.

***

Later, when they’re lying in bed letting the sweat cool against their skin, the world slowly sinking back into focus, Oswald asks, “What are we doing, Jim?”

Jim is laying behind Oswald, his arm draped over his hip, fingers playing with the silky fabric of the gown. He squeezes Oswald more securely against his chest, presses a kiss into the back of his head.

“Walking with a friend.”

**Notes for the Chapter:**

> Thank you to Deathbyotpin123 (https://deathbyotpin123.tumblr.com/) for creating the amazing illustration of Jim and Oswald up there. You are SO AMAZING!! <3 I can't put to words how much I love it!

**Author's Note:**

> Oswald's Lingerie in chapter 1 is inspired by these two items: 
> 
> https://www.lingeriediva.com/collections/mens-lingerie/products/micro-mini-hose-short?variant=7565160742942  
> https://www.lingeriediva.com/collections/mens-lingerie/products/black-stretch-lace-mini-short?variant=7565576667166


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